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WO2006029056A1 - Preparation d'olmesartan medoxomil - Google Patents

Preparation d'olmesartan medoxomil Download PDF

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Publication number
WO2006029056A1
WO2006029056A1 PCT/US2005/031481 US2005031481W WO2006029056A1 WO 2006029056 A1 WO2006029056 A1 WO 2006029056A1 US 2005031481 W US2005031481 W US 2005031481W WO 2006029056 A1 WO2006029056 A1 WO 2006029056A1
Authority
WO
WIPO (PCT)
Prior art keywords
olmesartan medoxomil
acid
water
solution
organic solvent
Prior art date
Application number
PCT/US2005/031481
Other languages
English (en)
Inventor
Lilach Hedvati
Gideon Pilarsky
Original Assignee
Teva Pharmaceutical Industries Ltd.
Teva Pharmaceuticals Usa, Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Teva Pharmaceutical Industries Ltd., Teva Pharmaceuticals Usa, Inc. filed Critical Teva Pharmaceutical Industries Ltd.
Priority to CA002573800A priority Critical patent/CA2573800A1/fr
Priority to EP05797758A priority patent/EP1706401A1/fr
Priority to JP2006538570A priority patent/JP4511550B2/ja
Publication of WO2006029056A1 publication Critical patent/WO2006029056A1/fr
Priority to IL181549A priority patent/IL181549A0/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings

Definitions

  • the present invention relates to processes for preparing olmesartan medoxomil.
  • olmesartan medoxomil is 4-(l -hydroxy- 1 -methylethyl)-2- propyl-l-[[2'-(lH-tetrazol-5-yl)[l,r-biphenyl]-4-yl]methyl]-lH-imidazole-5-carboxylic acid (5-methyl ⁇ 2-oxo-l,3-dioxol-4-yi)methyl ester (Merck Index 13th ed.).
  • the empirical formula is C 29 H 30 N 6 O 6 .
  • the molecular weight is 558.58.
  • Olmesartan medoxomil is a prodrug that is hydrolyzed during absorption, and it is a selective ATi subtype angiotensin II receptor antagonist.
  • Olmesartan medoxomil is disclosed by U.S. Patent No. 5,616,599 to Yanagisawa et al. It is marketed as BENICAR® in film- coated tablets of 5 mg, 20 mg, and 40 mg for treatment of hypertension in a human.
  • ODM-Mod olmesartan medoxomil
  • Step (vi) (the deprotection step) of the prior art synthesis is illustrated as follows:
  • Example 61(b) of the '599 patent discloses a process for preparing crude olmesartan medoxomil from a mixture of trityl olmesartan medoxomil (MTT) and aqueous acetic acid. Col. 176, lines 24-37. Triphenyl carbinol (TPC) is removed, and olmesartan medoxomil is isolated by evaporation. in solution
  • the impurity OLM-acid is also formed during the reaction by hydrolysis of the ester bond.
  • the prior art process yields crude olmesartan medoxomil containing 2.2% OLM-acid per area percent HPLC.
  • the present invention provides a process for preparing olmesartan medoxomil including the steps of: contacting trityl olmesartan medoxomil with an acid in a water miscible organic solvent, with or without water, preferably acetone and water, to obtain a solution of olmesartan medoxomil and a precipitate of triphenyl carbinol; separating the precipitate of triphenyl carbinol from the solution of olmesartan medoxomil; and contacting the solution of olmesartan medoxomil with a base to obtain a precipitate of olmesartan medoxomil.
  • the present invention provides a process for preparing olmesartan medoxomil including the steps of: contacting trityl olmesartan medoxomil with an acid in a water miscible organic solvent, with or without water, to obtain a solution of olmesartan medoxomil and a precipitate of triphenyl carbinol; separating the precipitate of triphenyl carbinol from the solution of olmesartan medoxomil; and contacting the solution of olmesartan medoxomil with a base to obtain a precipitate of olmesartan medoxomil.
  • Preferred water miscible organic solvents include, but are not limited to, acetone, acetonitrile, and t-butanol. Acetone is especially preferred.
  • the trityl olmesartan medoxomil is contacted with a mixture of a water miscible organic solvent and water. Most preferably, the trityl olmesartan medoxomil is contacted with a mixture of acetone and water.
  • the ratio of water to the water miscible organic solvent e.g., acetone, is preferably about 1 :3 to about 3:1 by volume.
  • the acid that is contacted with the trityl olmesartan medoxomil removes the triphenyl carbinol to form an acid salt of olmesartan medoxomil.
  • the acid is a strong acid having a pH of about 0 to about 4.
  • Suitable acids include, but are not limited to, organic acids such as formic acid, acetic acid, benzoic acid, and oxalic acid; oxoacids such as perchloric acid, chloric acid, chlorous acid, hypochlorous acid, sulfuric acid, sulfurous acid, p-toluene sulfonic acid, nitric acid, nitrous acid, phosphoric acid, and carbonic acid; and binary acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, hydrocyanic acid, and hydrosulfuric acid. Hydrochloric acid, p-toluene sulfonic acid, and especially sulfuric acid are preferred.
  • the amount of acid is about 2 to about 8 equivalents, more preferably about 3 to about 4 equivalents, and most preferably about 3 equivalents.
  • the temperature is preferably about 10°C to about 60°C, more preferably about 40°C.
  • the combination of trityl olmesartan medoxomil, the water miscible organic solvent, and the acid is maintained for about 3 to about 15 hours.
  • the combination is maintained for about 4 to about 6 hours, most preferably for about 4 hours.
  • water is added prior to separating the triphenyl carbinol to avoid the formation of undesired by-products.
  • the amount of added water is about 2 volumes per gram of trityl olmesartan medoxomil. Precipitation can be perceived visually as a clouding of the solution or formation of distinct particles of the precipitate suspended in the solution or collected at the bottom the vessel containing the solution.
  • Separating the triphenyl carbinol from the solution can be performed by any means known in the art, such as filtration or centrifugation.
  • Suitable bases include, but are not limited to, alkali and alkaline earth metal hydroxides, carbonates, and hydrogen carbonate salts.
  • Specific exemplary bases include, but are not limited to, sodium hydroxide, potassium hydroxide, calcium hydroxide, magnesium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, and calcium carbonate. Potassium carbonate and especially sodium bicarbonate are preferred.
  • the equivalents of base used is about equal to the equivalents of acid used, that is, the amount of base used is preferably about 0.8 to 1.5 equivalents compared to the amount of acid used.
  • the base preferably increases the pH of the solution, but the solution need not reach a basic pH.
  • the solution is preferably maintained at a temperature of about 2 0 C to about 25 0 C, preferably at about room temperature.
  • room temperature refers to a temperature of about 2O 0 C to 3O 0 C, preferably 2O 0 C to 25 0 C.
  • the solution is maintained until olmesartan medoxomil is precipitated.
  • the precipitate of olmesartan medoxomil can then be recovered by any means known in the art, such as filtration or centrifugation. Olmesartan medoxomil is recovered in its free base form, i.e., the nitrogen on the tetrazole is free.
  • reaction progress can be detected by any method known in the art, such as, for example, HPLC, GC, TLC, NMR, and mass spectroscopy.
  • olmesartan medoxomil can be obtained directly, without the evaporation step required by the prior art process, which is an inconvenient industrial method. See U.S. Patent No. 5,616,599 Example 61(b). Also, the product of the '599 process is obtained in a gel-like form, which is difficult to handle in an industrial process. In addition to presenting industrial disadvantages, the '599 process achieves a lower yield than that obtained by the present invention. Additionally, the olmesartan medoxomil obtained according to the present invention has a lower amount of the impurity olmesartan acid (OLM-acid).
  • Crude olmesartan medoxomil prepared according to the '599 process contains 2.2% OLM-acid.
  • crude olmesartan medoxomil prepared according the present invention contains less than about 1% OLM-acid, e.g., only about 0.89% OLM-acid. All percentages of impurities described herein are provided as area percentage HPLC at 220 nm.
  • Example 2 Preparation of crude olmesartan medoxomil A lL reactor, equipped with mechanical stirrer and thermometer, was charged with MTT (70 g), acetone (140 ml), water (140 ml), and H 2 SO 4 (19.47 g). The reactor was heated to 40°C for 2.5 hrs (at EOR, MTT is LT 1%). Water (140 ml) was added at 40°C, and the reaction was stirred for 1.5 hrs or until MTT is LT 0.1%. After cooling to 15°C and stirring for 1 hr, the TPC was filtered and washed with water (70 ml).

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention concerne un procédé pour préparer de l'olmésartan médoxomil.
PCT/US2005/031481 2004-09-02 2005-09-02 Preparation d'olmesartan medoxomil WO2006029056A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
CA002573800A CA2573800A1 (fr) 2004-09-02 2005-09-02 Preparation d'olmesartan medoxomil
EP05797758A EP1706401A1 (fr) 2004-09-02 2005-09-02 Preparation d'olmesartan medoxomil
JP2006538570A JP4511550B2 (ja) 2004-09-02 2005-09-02 オルメサルタンメドキソミルの調製法
IL181549A IL181549A0 (en) 2004-09-02 2007-02-26 Preparation of olmesartan medoxomil

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US60643704P 2004-09-02 2004-09-02
US60/606,437 2004-09-02

Publications (1)

Publication Number Publication Date
WO2006029056A1 true WO2006029056A1 (fr) 2006-03-16

Family

ID=35462159

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2005/031481 WO2006029056A1 (fr) 2004-09-02 2005-09-02 Preparation d'olmesartan medoxomil

Country Status (7)

Country Link
US (1) US7528258B2 (fr)
EP (1) EP1706401A1 (fr)
JP (1) JP4511550B2 (fr)
CN (2) CN1993355A (fr)
CA (1) CA2573800A1 (fr)
IL (1) IL181549A0 (fr)
WO (1) WO2006029056A1 (fr)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007017135A3 (fr) * 2005-07-29 2007-04-12 Krka Procede de preparation d'olmesartane medoxomil
EP1816131A1 (fr) * 2006-02-06 2007-08-08 KRKA, tovarna zdravil, d.d., Novo mesto Procédé pour la préparation du olmesartan medoxomil
EP2022790A1 (fr) * 2007-08-08 2009-02-11 LEK Pharmaceuticals D.D. Procédé pour la préparation ou la purification d'olmésartan médoxomil
WO2009019303A2 (fr) 2007-08-08 2009-02-12 Lek Pharmaceuticals D.D. Procédé de préparation ou de purification de l'olmésartan médoxomil
WO2010126013A1 (fr) 2009-04-28 2010-11-04 第一三共株式会社 Procédé de production de l'olmésartan médoxomil
WO2010126014A1 (fr) 2009-04-28 2010-11-04 第一三共株式会社 Nouveaux cristaux solvates
WO2010134052A1 (fr) * 2009-05-20 2010-11-25 Ranbaxy Laboratories Limited Procédé pour la préparation d'olmésartan médoxomil
CZ303188B6 (cs) * 2010-10-29 2012-05-16 Zentiva, K.S. Zpusob výroby olmesartanu medoxomilu
US8735598B2 (en) 2008-06-09 2014-05-27 Daiichi Sankyo Company, Limited Method for producing 1-biphenylmethylimidazole compound

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060281800A1 (en) * 2005-04-12 2006-12-14 Glenmark Pharmaceuticals Limited Polymorphic form of olmesartan and process for its preparation
WO2011014611A2 (fr) * 2009-07-30 2011-02-03 Dr. Reddy's Laboratories Ltd. Préparation de l'olmésartan médoxomil
AU2010277221A1 (en) * 2009-07-31 2012-03-15 Ranbaxy Laboratories Limited Polymorphic form of olmesartan medoxomil
EP2409710A1 (fr) 2010-06-29 2012-01-25 NanotecMARIN GmbH Matériau injectable et matériau à utiliser en tant que médicament ou complément alimentaire pour la prophylaxie ou le traitement de l'ostéoporose
EP2409682A1 (fr) 2010-07-19 2012-01-25 Werner E. G. MÜLLER Nano et microparticules se liant à l'hydroxyapatite pour la prophylaxie de caries et réduction de l'hypersensibilité dentaire
KR101266224B1 (ko) 2010-09-02 2013-05-21 일동제약주식회사 트리틸 올메사르탄 메독소밀의 개선된 제조방법
AR083523A1 (es) 2010-10-29 2013-03-06 Interquim Sa Procedimiento de obtencion del olmesartan medoxomilo
EP2489346A1 (fr) 2011-01-26 2012-08-22 NanotecMARIN GmbH Complément alimentaire et matériau injectable pour la prévention et le traitement de l'ostéoporose et autres maladies osseuses
EP2739619B1 (fr) 2011-08-05 2015-09-16 Lupin Limited Procédé de préparation d'olmésartan médoxomil
CN102558161B (zh) * 2011-12-07 2016-07-06 浙江华海药业股份有限公司 一种采用丙酮与水混合液精制奥美沙坦酯的工艺
CN102584804B (zh) * 2011-12-13 2016-05-18 浙江华海药业股份有限公司 一种三苯甲基奥美沙坦酯脱保护基制备奥美沙坦酯的工艺
US9034874B2 (en) 2012-07-20 2015-05-19 Novartis Ag Carbamate/urea derivatives
WO2014036686A1 (fr) * 2012-09-04 2014-03-13 上海迪赛诺化学制药有限公司 Procédé de préparation d'olmésartan médoxomil
CN108658954A (zh) * 2018-06-12 2018-10-16 广州小桔生物科技有限公司 一种高纯度奥美沙坦酯的精制方法
CN109761966A (zh) * 2019-01-30 2019-05-17 浙江省食品药品检验研究院 一种奥美沙坦酯晶体及其制备方法
CN111170946B (zh) * 2020-03-16 2022-02-11 浙江华洲药业有限公司 一种奥美沙坦中间体的合成方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5616599A (en) * 1991-02-21 1997-04-01 Sankyo Company, Limited Angiotensin II antagosist 1-biphenylmethylimidazole compounds and their therapeutic use
EP1555260A1 (fr) * 2003-11-28 2005-07-20 Dipharma S.p.A. Composes du phényltétrazole

Family Cites Families (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5138069A (en) * 1986-07-11 1992-08-11 E. I. Du Pont De Nemours And Company Angiotensin II receptor blocking imidazoles
DE3634717A1 (de) * 1986-10-11 1988-04-14 Dynamit Nobel Ag Verfahren zur herstellung von 5-methyltetrazol
US4870188A (en) 1987-04-16 1989-09-26 Neorx Corporation Vinyl substituted radiohalogen conjugates for protein labeling
US4870186A (en) * 1987-05-22 1989-09-26 E. I. Du Pont De Nemours And Company Tetrazole intermediates to antihypertensive compounds
DE4036706A1 (de) * 1990-11-17 1992-05-21 Hoechst Ag Verfahren zur behandlung der cardialen sowie der vasculaeren hypertrophie und hyperplasie
US5656650A (en) * 1990-12-14 1997-08-12 Smithkline Beecham Corp. Angiotensin II receptor blocking compositions
IE914572A1 (en) * 1991-01-17 1992-07-29 Zeneca Ltd Chemical process
US5614519A (en) * 1991-02-06 1997-03-25 Karl Thomae Gmbh (1-(2,3 or 4-N-morpholinoalkyl)-imidazol-4-yl)-benizimidazol-1-yl-methyl]-biphenyls useful as angiotensin-II antagonists
CA2229000C (fr) * 1991-02-21 2002-04-09 Sankyo Company, Limited Derives de 1-biphenylimidazole, leur preparation et leur utilisation therapeutique
US5252753A (en) * 1991-11-01 1993-10-12 Ortho Pharmaceutical Corporation Process for the preparation of certain substituted biphenyl tetrazoles and compounds thereof
US5310928A (en) * 1991-11-18 1994-05-10 E. I. Du Pont De Nemours And Company Process for preparing biphenyltetrazole compounds
US5264447A (en) * 1992-09-01 1993-11-23 Merck & Co., Inc. Angiotensin II antagonist
JPH06298683A (ja) 1993-04-15 1994-10-25 Sankyo Co Ltd 光反応による４−（２−置換）フェニルベンジルブロミド類の製造法
US5721263A (en) * 1993-06-07 1998-02-24 Takeda Chemical Industries, Ltd. Pharmaceutical composition for angiotensin II-mediated diseases
JPH0753489A (ja) 1993-06-11 1995-02-28 Sankyo Co Ltd ビフェニルカルボキサミド誘導体の製造法
US5412102A (en) 1994-05-27 1995-05-02 Syntex (U.S.A.) Inc. Processes for preparing 1-butyl-2-[2'-(2H-tetrazol-5-yl) biphenyl-4-ylmethyl]-1H-indole-3-carboxylic acid
JP2928982B2 (ja) * 1994-10-27 1999-08-03 住化ファインケム株式会社 ４’−ブロモメチル−２−シアノビフェニルの製造法
JPH08325248A (ja) 1995-05-26 1996-12-10 Chugoku Kayaku Kk テトラゾール類の新規な合成試薬及びそれを用いたテトラゾール類の製造方法
US5994348A (en) * 1995-06-07 1999-11-30 Sanofi Pharmaceutical compositions containing irbesartan
JP3671266B2 (ja) * 1996-03-21 2005-07-13 東洋化成工業株式会社 ５−置換テトラゾール類の製造方法
GB9613470D0 (en) 1996-06-27 1996-08-28 Ciba Geigy Ag Small solid oral dosage form
IT1291551B1 (it) * 1997-04-11 1999-01-11 Luso Farmaco Inst Processo per la preparazione di composti 4-bromometil bifenilici
FR2771090B1 (fr) * 1997-11-17 2000-02-04 Sanofi Sa Procede de preparation de derives de bromomethyl-biphenyle
DE19757995A1 (de) 1997-12-29 1999-07-08 Great Lakes Chem Konstanz Gmbh Verfahren zur Herstellung von aromatischen Brommethyl-Verbindungen
JP4185182B2 (ja) 1998-04-08 2008-11-26 第一三共株式会社 イミダゾール誘導体の製造方法
JP4260241B2 (ja) 1998-04-21 2009-04-30 第一三共株式会社 イミダゾール誘導体の製造法
US6271418B1 (en) * 2000-02-22 2001-08-07 Nippon Kayaku Co., Ltd. Process for preparing (hetero) aromatic substituted benzene derivatives
AU1432402A (en) * 2000-11-21 2002-06-03 Sankyo Co Medicinal compositions
ES2299616T3 (es) * 2002-06-12 2008-06-01 Sumitomo Chemical Company, Limited Procedimiento para producir 4'-bromometil-2-cianobifelino.
CN1271068C (zh) 2003-03-25 2006-08-23 上海医药工业研究院 一种奥美沙坦酯的制备方法

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5616599A (en) * 1991-02-21 1997-04-01 Sankyo Company, Limited Angiotensin II antagosist 1-biphenylmethylimidazole compounds and their therapeutic use
EP1555260A1 (fr) * 2003-11-28 2005-07-20 Dipharma S.p.A. Composes du phényltétrazole

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
LARSEN R D ET AL: "Efficient Synthesis of Losartan, A Nonpeptide Angiotensin II Receptor Antagonist", JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY. EASTON, US, vol. 59, no. 21, 21 October 1994 (1994-10-21), pages 6391 - 6394, XP002097895, ISSN: 0022-3263 *

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EA014026B1 (ru) * 2005-07-29 2010-08-30 Крка, Товарна Здравил, Д.Д., Ново Место Способ получения олмесартан медоксомила
WO2007017135A3 (fr) * 2005-07-29 2007-04-12 Krka Procede de preparation d'olmesartane medoxomil
US7943779B2 (en) 2005-07-29 2011-05-17 Krka Process for the preparation of olmesartan medoxomil
EP1816131A1 (fr) * 2006-02-06 2007-08-08 KRKA, tovarna zdravil, d.d., Novo mesto Procédé pour la préparation du olmesartan medoxomil
US8592474B2 (en) 2007-08-08 2013-11-26 Lek Pharmaceuticals D.D. Process for the preparation or purification of olmesartan medoxomil
WO2009019303A3 (fr) * 2007-08-08 2009-04-02 Lek Pharmaceuticals Procédé de préparation ou de purification de l'olmésartan médoxomil
WO2009019303A2 (fr) 2007-08-08 2009-02-12 Lek Pharmaceuticals D.D. Procédé de préparation ou de purification de l'olmésartan médoxomil
EP2022790A1 (fr) * 2007-08-08 2009-02-11 LEK Pharmaceuticals D.D. Procédé pour la préparation ou la purification d'olmésartan médoxomil
US8735598B2 (en) 2008-06-09 2014-05-27 Daiichi Sankyo Company, Limited Method for producing 1-biphenylmethylimidazole compound
WO2010126013A1 (fr) 2009-04-28 2010-11-04 第一三共株式会社 Procédé de production de l'olmésartan médoxomil
WO2010126014A1 (fr) 2009-04-28 2010-11-04 第一三共株式会社 Nouveaux cristaux solvates
KR20120006512A (ko) 2009-04-28 2012-01-18 다이이찌 산쿄 가부시키가이샤 올메살탄메독소밀의 제조 방법
US8859600B2 (en) 2009-04-28 2014-10-14 Daiichi Sankyo Company, Limited Acetone solvate crystals of trityl olmesartan medoxomil
US8933241B2 (en) 2009-04-28 2015-01-13 Daiichi Sankyo Company, Limited Method for producing olmesartan medoxomil
WO2010134052A1 (fr) * 2009-05-20 2010-11-25 Ranbaxy Laboratories Limited Procédé pour la préparation d'olmésartan médoxomil
CZ303188B6 (cs) * 2010-10-29 2012-05-16 Zentiva, K.S. Zpusob výroby olmesartanu medoxomilu

Also Published As

Publication number Publication date
CN1976926A (zh) 2007-06-06
US7528258B2 (en) 2009-05-05
JP2007509992A (ja) 2007-04-19
JP4511550B2 (ja) 2010-07-28
EP1706401A1 (fr) 2006-10-04
CA2573800A1 (fr) 2006-03-16
CN1993355A (zh) 2007-07-04
IL181549A0 (en) 2007-07-04
US20060069141A1 (en) 2006-03-30

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